Success at Work, Failure at Home

One of the differences between being a CEO and a venture capitalist is that I obviously meet with many more CEOs now than I did then. As such, it has become more apparent that many of my struggles as a CEO are surprisingly common. One observation that stands out, probably because it is rarely discussed, is how many founder/CEOs have relationship struggles with their significant others and families. For me, the brightest years at IronPort were without a doubt the darkest years at home. While I was focused, motivating, articulate, and decisive at work, I was inconsiderate, preoccupied, self-centered, and lazy at home.

Now, having worked through that time with my family, I’m in a much better place to reflect on what happened, how I could have handled things differently, and offer some advice to other founders who may be caught up in a similar dynamic.

As a first time founder/CEO, I really had no idea what I was doing. Sure, I had gone to business school, worked at plenty of large companies and even other successful startups, but nothing prepared me for the incredible stress and overwhelming life focus of actually running a startup.

I did my best to move up the learning curve: I surrounded myself with great mentors, board members, coaches, and, most importantly, the challenging, wicked smart executive team members that worked with me everyday. We definitely made lots of mistakes, but we did many things right and IronPort grew to be a very large and successful company over the seven years before we ultimately sold to Cisco in 2007. All that said, I believe I could have been a much more effective leader if I had leaned in at home. As my relationship with my family deteriorated, so did my concentration at work as I was constantly trying to manage it in fits and starts. Here are some details of my personal struggle:

Part of the magic of a startup is the fear of death. You have only so much money in the bank, and if you don’t get to the right milestone before you run out, then you’re dead—company goes under, it’s over. There’s a way to cheat death when you are not going to make it—you sound the alarm and force everyone to code through the night and/or weekend. This is stereotypically the life one signs up for at an early stage tech startup. Get in early, kill yourself with a team making something great, and get a meaningful product out before you run out of money. And hopefully, make it up to that hardworking team with stock options later.

I didn’t code, but as the CEO, I felt it necessary to be there physically with the engineering team. I would sit through architecture discussions, product reviews, and wireframe layouts. Sometimes, I would just get everyone lunch or dinner. When we started pulling consistent coding weekends, we brought in the entire management team to serve the engineers: We brought them food, washed their cars, got oil changes, took in their dry cleaning, and arranged for childcare for their kids in the office. Lead by example, lead from the front, was the CEO approach I convinced myself was necessary.

Now contrast this with my home life.

One of the stated values at IronPort was “work/life balance,” but I clearly wasn’t living it. I was rarely home. And when I was home, well, let’s just say I wasn’t particularly helpful or cheery. My perspective at the time was: I’m killing myself at work, so when I get home, I just want to kick back with a cocktail and watch some TV. All I do is talk to people all day long and so at home, I’d really prefer not to talk much, just relax.

This posture was, of course, completely opposite to how my wife felt. After having left her VP role in a successful startup, she was now home speaking in monosyllabic words to kids all day and was starving for adult conversation when I got in the door. And that part about sitting on my ass in front of the TV with a cocktail? This ran counter to all of her efforts to teach the kids about pitching in as a family. The message of everyone helping to cook, clean, and be responsible for the household fell completely flat when daddy wouldn’t so much as take out the trash or change a light bulb. Nope, I was far too important for that and suggested she should hire someone to keep the house clean or even cook, if that was “stressing her out”.

Ugh. I was completely missing the point and talking past her… I was setting such a great example at work, but such a terrible one at home where I often acted like a self-important asshole.

As IronPort grew, I was constantly on the road with customers, press, analysts, and of course, recruiting and energizing employees. We ultimately did over 60% of our revenue outside of the U.S., and we all felt it very important to support all of our disparate offices from Europe to Asia to South America. There were times in a given month when I was gone 50-75% of the days. Even when I was home, I was usually in this brutal state of sleep deprivation and recovery from adjusting to yet another time zone. While I was gone, 100% of the daily burden fell on my spouse, usually resulting in a solid week of arguments upon my return. I started referring to the week after a long trip as “re-entry”, like John Glenn’s Friendship Seven fireball.

After years of working full-time with our first child, and part-time after our second, my Harvard MBA wife, who had had an amazing career in her own right, “decided” to become a full-time mom and take care of our children shortly after our third was born. I say “decided” because at the time, it was clear to both of us that I wasn’t willingly scrubbing in as a 50/50 partner at home. She endured the rocky years while I was running IronPort, but insisted that when it was over, we were going to re-evaluate and recalibrate.

I took about 18 months off in between IronPort and joining Andreessen Horowitz. During that time, I was packing lunches, driving carpools, and making dinners, and began doing my real part in the family. With the help of my wife and other role-model dads, I essentially got re-programmed and it has continued to work for us even though I’m working full-time again. Now one might say that being a partner at a VC firm, even a hard working one, isn’t the same as being a founder/CEO of a startup… I’ll admit that’s true. However, now that I’m on the other side, I believe that I could have coached my former CEO self to success as well. Here are the most critical things I needed to change:

Disconnect to Connect. Although it’s easy for me to see it now, at the time I clearly thought what I was doing at work was far more important and urgent than what was going on at home. It sounds weird now, but this required a real mindset change for me. My wife dropped a bunch of hints (e.g. “How did I suddenly land in a 1950’s relationship?!”), but I was undeterred in the thick of it. The shock of almost losing the relationship made me pay more attention, but I was only going through the motions with my mind still firmly attached to the business. I believe the change in attitude came from truly connecting and tuning in at home. This required disconnecting from work (e.g. turning off the computer and phone), and completely focusing all of my attention on the details of the home. Cooking a great meal. Helping with a science project. Discussing the future with my partner. I was often rightly accused of being physically present without being mentally present. If you find yourself sneaking into the bathroom to complete emails, then you’re certainly not in the moment… Getting some time physically out of the Silicon Valley pressure cooker was also helpful in changing my perspective.

Participate. It’s just not possible to be a real partner if you aren’t materially participating. I believe even the busiest CEOs must drive a carpool, pack a lunch, help with homework, make a breakfast or dinner, and consistently attend school events. Being involved every week is the only way to stay connected at home, and it cannot be outsourced. No matter how exhausted I am from traveling, I push myself to “not be lazy” at home—it’s just too important. When you are involved, there is a natural cadence to planning the week together and communication improves dramatically.

Communicate. Multiple, daily phone and text check-ins are the norm now, but not then. When I was traveling at IronPort, I would sometimes go for days without communicating at all. Now that I am completely tuned in to the weekly family schedule, we plan and calendar family meals (perhaps the single most important thing we do), pickups and drop-offs, and make adjustments on the fly. E.g. Did some time suddenly free up so I can complete an errand? Can I pick something up on the way home? Etc. My norm is to check in between meetings, but if I’m the “parent on duty”—i.e., if my wife is out of town—then I will start a meeting with, “You’ll have to excuse me, but I’m the parent in town so I need to keep my phone handy in case of an issue.” Communication was by far my biggest area for improvement.

Planning and Priorities. My wife and I have a weekly date night. My son and I are in a fantasy football league together. I cook with my daughters. Most times these have become immovable appointments on my calendar. There is a phrase—“truth in calendaring”—if something is important, then you must carve out time in your life to do it. When my calendar reflects that I can’t do a meeting on Wednesday and Friday mornings before 9am, because I cook breakfast and drive a carpool, then it’s amazing how meetings just don’t get scheduled. If at all possible, living physically close to the office is also a huge help to juggling the priorities. It means that I can cut out for a family dinner and then go back to the office or have a late meeting afterwards.

In retrospect, I believe that I could convince the hardest working CEOs that having some real life balance by investing in your important relationships will make you a better CEO. When you are out of balance, it affects your stress, judgment, and ultimately becomes another destabilizer just when you need to be the most put together. I also believe this change is actually a much better example of leadership than the one I was exuding. When a leader shows the way toward getting things done and balancing their life, it sets a much better example for everyone else in the company who struggle with it too.

Great post and I’m glad you wrote it. Ive seen far too many guys have their home lifes explode running startups. Your point about disconnecting from email is huge, and something I put into place years ago, and has worked wonders.

I just wanted to say that I liked this post very much. As the wife of a CEO/Founder I see ourselves reflected in this reading and I’m greatful that someone out there came out and told things exactly as they are. Before reading this I felt as our family was the only one going thru this, but as I continue reading I noticed there are more people in this situation. Now I’m more able to understand my husband and being more supported of his work as well as working with him towards a better relationship and a more quality time as a family. Thx Scott.

Very thoughtful perspective. It’s nice to see a successful person reflect on how he could’ve done it better in the past. Good for you for being so candid and allowing others to benefit from what you’ve learned. By the way, this is the first time I’ve commented online on a post.

All true. These scenarios reminds me of Steve Jobs in the other room boasting about the new Apple HQ not even bothering to invite his daughter in, whom he knew was an aspiring architectural engineer. At least that’s what the auto bio said. For me, I’ve experienced this on a premarital level and it has made me very cautious about the future. You either learn from your mistakes, and the mistakes of others, otherwise you waste experiences.

So True. One thing I would add as a serial startup/entrepreneur is that the style of conversation that helps drive interaction, trust, and motivation within a business and its employees doesn’t translate completely with a person you have an intimate, loving, sensual, and sentimental obligation to.

Some things do translate well. For instance the patience and even keeled temperament required to maintain a level of respect and openness is important to both wok and home lives. On the other hand the levels of distance and tone can have a stark difference between the two environments.

As an example, working on an emotional issue with a significant other doesn’t work well with checkins, progress updates, and check lists (which can be cold to a person you sleep next to every night) and focusing deeply on emotions doesn’t work when communicating clear objectives and goals with peers and employees (that you hopefully don’t sleep next to – ever). Again, there is some overlap, but the differences are monumental.

Being a startup guy in a relationship is a constant lesson in understanding those differences; not focusing on “optimizing” for your relationship but simply nurturing it together ;)

This is such a great post. I’ve heard tons of people say that they wish they spent more time with their family, but I haven’t seen it so well articulated. As I sit working from home in a huge snowstorm, I think of the people who trudged into work ignoring their own personal safety and will gladly take a few minutes to play with my daughter when she wakes up from her nap!

As one of your engineers during that time, your commitment to “being around for the team” really resonated. It has been a rarity in a lot of the companies I’ve worked for since, and it makes all the difference to the team, even if it’s only a difference of perception…

Hmm it seems like your site ate my first comment (it was extremely long)
so I guess I’ll just sum it up what I had written and say, I’m thoroughly enjoying your blog.
I as well am an aspiring blog blogger but I’m still new to the whole thing.

Do you have any tips for beginner blog writers?
I’d really appreciate it.